Top 10 Bob Dylan Songs, From Great to Absolute Classic

FRIDAY, MARCH 31, 2017 |

Posted by: Robert Steiner

For a guy halfway into his 70s, Bob Dylan has been keeping busy, and the music legend shows little sign of slowing down any time soon. He's currently in the midst of a seemingly endless world tour, he's finally picking up the Nobel Prize he won during his tour stop in Stockholm, and today, he dropped his brand new album Triplicate. The massive triple-album will consist entirely of standards and classics within the Great American Songbook, but it's not like Dylan of all people has ever had a shortage of original songs. In fact, the man quite possibly has one of the most impressive and influential bodies of work of any songwriter of the past century; so in other words, picking ten of his best songs was almost goddamn impossible. This was easily the hardest thing I've done all week, and there were many, many drafts of this list. There way truly no way to get this right for everyone, but it was certainly worth giving it a shot, so here are 10 Dylan songs that I think stand out from the rest.

But first, because not having them on the list already feels like a crime, a quick shout-out to the honorable mentions: "Hurricane," "Knockin' On Heaven's Door," "It Ain't Me Babe," "The Lonesome Death of Hattie Carroll," "Chimes of Freedom," "Things Have Changed," "Ballad of a Thin Man," "Mr. Tambourine Man," and "Positively 4th Street." Look at that, one more song and you got another list. But for now, on with the main 10:

10. SUBTERRANEAN HOMESICK BLUES (Bringing It All Back Home, 1965)

Let's get this out of the way right now: Anyone who says this is the first rap song has no effing idea what they're talking about. That said, "Subterranean Homesick Blues" is still a milestone for Dylan, as it was the frantic opener to his first all-electric album, and inspired one of the earliest forms of a music video with the now iconic note-cards-in-an-alley scene. You can definitely tell this was the period he was hanging out with experimental beat poet Allen Ginsburg, but Dylan still manages to paint a vivid and compelling musical journey even without making much sense at all.

9. ALL ALONG THE WATCHTOWER (John Wesley Harding, 1967)

There's no denying Jimi Hendrix is the one people think of when the harrowing tale of jokers, thieves, and princes comes to mind, and for good reason. Even though "Watchtower" inspired one of the greatest covers of all time, it would be foolish to forget the original's greatness in its own right, which best shows Dylan's ability to create a vast and full-fledged story in just two-and-a-half minutes. The three-chord vamp and relentless drumbeat makes it initially sound pretty unassuming compared to Hendrix's screaming electric epic, but Dylan's underscored version has its own crackling energy and emotional intensity that's the same feeling as riding through a dusty, ominous road alone at night.

8. DON'T THINK TWICE, IT'S ALRIGHT (The Freewheelin' Bob Dylan, 1963)

For all the Dylan songs you can dissect and pick apart and find 200 different meanings, there are also plenty of tracks that are simple, straightforward, and hit you square in your emotional core. "Don't Think Twice" is very clearly a breakup song, but it's one that perfectly captures that feeling of sadness over times that have passed while still keeping your head up for the memories to come. It's a gentle and bittersweet reminder to not dwell on what can't be changed, and instead keep moving forward without hesitation, which is something anyone who has fallen in and out of love with someone can undoubtedly relate to.

Alright, I'm going to cheat a little bit, but I really believe that these songs shine the brightest as a pair. Essentially the alleged bookends of Dylan's first marriage to his ex-wife Sara, "Johanna," though incredibly surreal, ultimately depicts Dylan longing for a love that isn't yet attainable, while "Idiot Wind" is possibly one of the most brutal divorce songs ever pressed on wax. With these songs nearly a decade apart, it's fascinating and somewhat saddening to think that the same woman that likely inspired "The ghost of electricity howls in the bones of her face / Where the visions of Johanna have not taken my place," also prompted the lines, "Idiot wind / Blowing every time you move your teeth / You're an idiot, babe / It's a wonder that you still know how to breathe." Dylan has always maintained he writes about what he's experienced, and these two songs in turn create a picture of him at his most personal and deeply vulnerable.

6. A HARD RAIN'S A-GONNA FALL (The Freewheelin' Bob Dylan, 1963)

The early 1960s were uncertain times in the US and all over the world, so Bob Dylan's dire warning of impending doom couldn't have come at a more fitting point. Along with Freewheelin's "Masters of War," Dylan solidified his role as the voice of the rising rebellious, idealistic youth movement, as well as a prophet for the rest of the war-torn and turbulent decade. "Hard Rain's" message of desperation and longing for change becomes all the more potent when you realize that less than five months after its release, the US became locked in the Cuban Missile Crisis, and mutually assured destruction seemed like a trigger-finger away. Better yet, you look at everything thats occurred this very decade, 50-plus years after the songs existence, one has to wonder if we'll ever heed the its message.

5. DESOLATION ROW (Highway 61 Revisited, 1965)

It's fitting that the closer to an album named after a highway is a near-12 minute marathon that feels like a long drive through a grim, barren wasteland. Even while Dylan was well into the "Electric" period of his career, he used this track to briefly return to his acoustic-folk roots, and in doing so, created an odd world populated by sullen biblical figures and down-and-out literary characters that has fascinated listeners for decades. It's a track that will leave you wondering if "Desolation Row" actually exists, but by the way Dylan uses his winding and complex lyrics to invoke a sense of anxious dread, you at least know its a place you'd be better off passing through.

4. TANGLED UP IN BLUE (Blood On The Tracks, 1975)

Blood On The Tracks will undoubtedly go down in history as one of the greatest breakup albums ever made, and this up-tempo opener is the center-piece of what makes this record so brilliant. This long and toiling account of being in the eye of a crumbling relationship shows Dylan's storytelling abilities at their absolute best. While yes, the narrative structure is all over the place, it still works as a flowing story thanks to Dylan's urgent and frantic vocal delivery, giving it the feeling of a distressed ex-lover in the middle of a panic attack. It's a track that captures Dylan at his most energetic, his most convicted, and as the title promises, his most distressingly blue.

3. BLOWIN' IN THE WIND (The Freewheelin' Bob Dylan, 1963)

It seems damn near impossible to capture the sentiment of an entire generation of people in under three minutes, and yet at the age of 22, Bob Dylan managed to do just that. The song that became one of the most celebrated anthems of the Civil Rights Movement, the feeling of frustration and determination mixed with optimism and perseverance rang true for the rest of the 60s, and continues to inspire people to invoke real change to this day. Even if Dylan never wrote a good song for the rest of this career, "Blowin' In The Wind" would still be considered the bar for all songwriters to match, and is easily one of the greatest protest songs ever written.

2. THE TIMES THEY ARE A-CHANGIN' (The Times they Are A-Changin', 1964)

"Blowin' In The Wind" is only one of the greatest protest songs ever written, and not the greatest protest song ever written, simply "Times" exists. Turns out the only person who can out-write Bob Dylan is Bob Dylan, and this stirring anthem is one of the early hits that put him on the map and proved that he was more than a Woody Guthrie knock-off. "The Times" was released within a climate clamoring for change, and like many of the songs of his protest period, it continues to inspire people across the world and across generations to hold onto hope, even in the darkest of hours, and bring on a better future.

1. LIKE A ROLLING STONE (Highway 61 Revisited, 1965)

Shocker, I know. This song has topped so many best of all time lists that there literally isn't anything more to say that hasn't already been said, although that in itself speaks volumes about the sheer greatness of this track. The premise of a formally rich brat getting kicked in the face by reality is an entertaining story enough on its own, but the tracks importance extends so much more beyond that. It was the manifesto of Dylan going electric, proving once and for all his folk protest days were long gone. It was the first song over four minutes to be a hit single, destroying the precedent that artists were confined to sub-three minute songs if they had any hope of getting radio play. Most importantly, it brought rock music to a completely new level of depth and sophistication by proving the genre could be more than just about girls and dancing, and actually take on complex themes and vivid stories with literary prowess and maturity. Music literally wasn't the same after "Like A Rolling Stone," and considering all the artists it inspired, music is all the better because of it.